Thermal and Photofragmentation of N-Benzoylhydrazone Derivatives

Two selected benzoylhydrazones I and II were subjected to thermolysis by reflux at 200 °C. Benzil, benzoic acid, biphenyl, benzanilide together with the corresponding ketones, nitriles and imines were isolated. Similar treatment of the third hydrazone III at 250 °C afforded, in addition to the previ...

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Bibliographic Details
Published in:Journal of the Chinese Chemical Society (Taipei) 1998-12, Vol.45 (6), p.767-772
Main Authors: Gaber, Abd El-Aal M., Mohamed, Shaaban K.
Format: Article
Language:English
Subjects:
Free radicals
N-Benzoylhydrazones
Photolysis
Thermolysis
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Summary:Two selected benzoylhydrazones I and II were subjected to thermolysis by reflux at 200 °C. Benzil, benzoic acid, biphenyl, benzanilide together with the corresponding ketones, nitriles and imines were isolated. Similar treatment of the third hydrazone III at 250 °C afforded, in addition to the previous products, bibenzyl, stilbene, and 2‐phenylindole. Photolysis of the same hydrazones I‐III in acetonitrile gave the previously reported products but in different ratios along with azine derivatives and substituted methanes. A free radical mechanism involving homolysis of the N‐N and C‐N bonds is suggested, substantiated by trapping of phenyl radical with isoquinoline, to account for the formation of the identified products.
ISSN:0009-4536
2192-6549
DOI:10.1002/jccs.199800115